Ethanol → HCID 19068781, compound

HRID 1957263Notes

Reaction equation

HRID 1957263 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([CH:23]=O)[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.[CH2:25]([OH:27])[CH3:26]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18](/[CH:23]=[CH:3]/[C:2]([O:27][CH2:25][CH3:26])=[O:1])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 186929322-Chloro-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]benzaldehyde

Product 1

HCID 19068781HCID 19068781, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1.35 g of sodium ethoxide in 20 ml of anhydrous ethanol was added dropwise to 4.0 g of 3-chloro-2-(4-chloro-3-formylphenyl)-5-trifluoromethylpyridine and 2.9 g of triethyl phosphonatoacetate in 70 ml of anhydrous toluene. After stirring at about 20° C. for 44 hours, the solvent was removed. The residue was taken up in 100 ml of 10% strength hydrochloric acid and extracted three times with 100 ml of ethyl acetate each time. The combined organic phases were washed with 100 concentrated. Chromatography on silica gel with cyclohexane/ethyl acetate (10:1) resulted in 3.4 g (71%) of colorless crystals; melting point: 118°-120° C.

Workup

  1. customthe solvent was removed
  2. extractionextracted three times with 100 ml of ethyl acetate each time
  3. washThe combined organic phases were washed with 100
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42a589cf91c6425baafb00b43ab60e9b
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

Loading…